1. MG BWhy It’s Cool: There are any number of MG Bs out there for $5000 or less. The question is, how much more will it take to get them running smoothly? If you sink $5000 just to put the car in your driveway, will you end up spending that much more to get it back out onto the road? Twice that much? Getting an inexpensive MG B can be like opening up Pandora’s box, except instead of all of the evils of the world escaping, it’s just a big puff of Lucas wiring smoke. Once that all clears though, you’re left with one of the best motoring experiences on the planet. Think of the cost as an investment towards future fun.
  2. Triumph SpitfireWhy It’s Cool: For what is considered a very small outlay in the classic car world, you too can be the proud new owner of a car with a name as cool as Spitfire. Much like the earlier MG B though, the initial purchase price of a Sptifire is more like an initial investment. If you like puzzles and treasure hunts, a Spitfire might be for you. And always remember the light at the end of the tunnel: days of open-top fun behind the wheel of an excellent British sports car.
  3. Datsun ZWhy It’s Cool: A quick eBay search reveals 41 Datsun Z-series cars for sale, with 24 of them landing at or below our $5000 limit. Surely there’s one in there that’s not a total basket case. Either way, for under five grand, there’s got to be at least one for you. The Z is often a blank canvas, ready to be transformed in one way or another.
  4. Citroen DSWhy It’s Cool: Well, unfortunately you missed the window to view this car at the Antique Car Show at Watson Lake in Prescott, Arizona. But we do know this: the car lives in Arizona, so it’s probably relatively rust-free. It has a sweet red velour-looking interior. Finally, it’s from 1965. Which is cool, until the hydraulic system goes, and you’re left yelling things in French at it until it bleeds itself dry. But come on, it’s a DS for $4500.
  5. 1966 Plymouth FuryWhy It’s Cool: This car’s paint looks nice, but the interior has probably seen better days. What were you expecting for well under half of our $5000 limit, though? It’s got a 318 under the hood and a clean title in the state of New Jersey. As long as Irene didn’t put it underwater, this could be the beginning of a fun project.